Mature Crossdressing Stories

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Infinite Scroll

Sexual Scenarios

by zig322 on Dec 7, 2019
Fan Fiction

What we have here is a series of sexual scenarios from anime, cartoons, comics, tv shows, video games, movies, and even some original ideas. These scenarios will involve: spanking, ENF, forced feminization and crossdressing, foot fetish, tickling, LGBTQ, mind control, incest, any other perverted thing anyone can think of, and of course sex (consent or non-co...

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In For a Penny...

by TheHellWasIThinking on Sep 15, 2017
Fetish

To the reader: After I'd finished this story, I didn't know where to put it. It contains elements of several Lit categories, and I probably could have put it in any one of them. In the end, I decided to put it in Fetish, although it's very much a Loving Wives tale, as you'll soon see. NOTE: Every word of this is true. (Except for "Every word of this is true...

Curse of the Living Clothes

by calx86 on Jan 8, 2020
Fantasy

There are several stories out there involving living clothes but I want to leave this open to allow many collective authors to be as creative as possible. For example, you can write a story about clothes simply coming to life and stripping their wearer, leaving them nude and embarrassed or maybe the living clothes forces someone to wear them and turns them i...

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Shemale Trouble

by Braids on Mar 11, 2007
Fetish

You were at a bar when it happened. You were just having a drink when a hot girl started hitting on you. You had nothing else better to do and you didn’t want to pass up an easy lay so you offered to take her back to your place for a little fun. She agreed without a question, but as you were walking out of the bar, you felt something hit the back of your hea...

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Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...

By the Grace of Guile

by komrad1156 on Sep 14, 2017
Transsexuals & Crossdressers

*Author's note: Several years ago, I read an interesting book by author Loyal Rue, a professor of Religion and Philosophy at Luther College, called By the Grace of Guile. An excerpt from one review says this: "For people who are troubled by a world increasingly filled with the sweet-talking duplicity of politicians, preachers, advertisers, and sundry huckste...

Life and Time of Lady Vargos Ch. 01

by rik581 on Oct 3, 2018
Transsexuals & Crossdressers

I am in the process of reposting my stories. *** "The Life and Times of Lady Vargos" is the second book of the Martin Hastings adventures into a life of forced feminization. This story follows the feminization and marriage of a reluctant young man as he is forced to accept his fate as a male/bride, in a same sex marriage, arranged by his family. This stor...

Taken by My Wife

by BlondeKaryn on Sep 12, 2017
Transsexuals & Crossdressers

My wife had recently found out about my crossdressing. She was a little upset at first, but then seemed to be more accepting of it as time went by. I came home from a business trip a couple of weeks ago to a welcome that I could never have imagined in my wildest dreams. I had taken quite a few of my clothes with me, and spent every minute possible on my tri...

Kissing Crossdressers Pt. 01

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

It started when Carla, my hot sexy wife went away on a spa break a few days with some of her girlfriends. Carla is 40 (I'm 48), has blonde hair, blue eyes, 34DD tits and a curvaceous ass. She works long hours in a busy office as a manager, I work in a local library and my job is far less stressful than hers. And her job has definitely taken its toll on our s...

Rm 209: First Sex as a Crossdresser

by MelissaMwaz on Sep 16, 2017
Transsexuals & Crossdressers

This is a TRUE STORY. I've been crossdressing for much of my life, as far back as I can remember. I would even go to sleep as a kid and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-...